CH259689A - Process for the preparation of a biguanide derivative. - Google Patents

Process for the preparation of a biguanide derivative.

Info

Publication number
CH259689A
CH259689A CH259689DA CH259689A CH 259689 A CH259689 A CH 259689A CH 259689D A CH259689D A CH 259689DA CH 259689 A CH259689 A CH 259689A
Authority
CH
Switzerland
Prior art keywords
preparation
chloro
biguanide derivative
acid
salts
Prior art date
Application number
Other languages
German (de)
Inventor
Limited Imperial Ch Industries
Original Assignee
Ici Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ici Ltd filed Critical Ici Ltd
Publication of CH259689A publication Critical patent/CH259689A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C07C279/26—X and Y being nitrogen atoms, i.e. biguanides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     Biguanidderivates.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung von     Nx-4-Chlor-3-          1#roniplienyl-N        @-n-propylbiguanid,    welches ein  wertvolles chemotherapeutisches Mittel ist oder  als Zwischenprodukt für die Herstellung von  chemotherapeutischen Mitteln verwendet wer  den kann. Es ist     insbesondere    ein wertvolles       Antimalariamittel.     



  Erfindungsgemäss wird die besagte neue  Verbindung,     nänilieh        Ni-4-Chlor-3-broinpheny        1-          N        '-n-propylbiguanid,    dadurch erhalten,     da13     man     N'-n-Propyldicy        andiamid    mit     4-Chlor-3-          bromanilin    umsetzt.  



  Die     Unisetzung    erfolgt zweckmässig durch  Erhitzen eines Salzes des Amins mit dem sub  stituierten     Dicyandiamid    in Gegenwart eines  Lösungsmittels, wie z. B. Wasser oder       Äthoxyäthanol.     



  Das     Nl-4-Chlor-3-bi-oniphen@-1-N'-ii-propy        1-          biguanid    stellt eine starke Base dar, welche  mit organischen und anorganischen Säuren  beständige Salze ergibt, die in manchen Fäl  len in Wasser     leielit    löslich sind. Die     Salze     lassen     sich    dadurch herstellen, dass die Base  in     wässrigen    Lösungen der Säure gelöst und  hierauf     (las    Wasser verdampft wird, doch  können sie in trockener Form bequemer durch  Vermischen der Komponenten in einem     orga-          nisehen    Lösungsmittel, wie z. B.

   Aceton,     ode@-          in    einem Alkohol, in     welehem    die Salze spär  lich löslich sind, hergestellt werden. Auf diese  Weise kann man beispielsweise die Salze mit  Essigsäure, Milchsäure,     Methansulfonsäure,            Methylendisalieylsäure,        lletliylen-bis        -(3-        oxy        -          na,phthoesäure    und Salzsäure bequem her  stellen.  



  Das folgende Beispiel diene zur Erläute  rung der Erfindung.  



  <I>Beispiel:</I>  Ein Gemisch von<B>1.3,9</B> Teilen     N@-n-Prop.##1-          dicyandiainid    und 24,3 Teilen     4-Chlor-3-          bronianilin-chlorhydra.t    in 75 Teilen     j3-Äthoxy-          ä        thanol    wird während 3 Stunden unter     Rück-          Euss    zum Sieden erhitzt. Hierauf lässt man  das Gemisch abkühlen, worauf     abfiltriert     wird. Der feste Rückstand wird mit kaltem       Äthylacetat    gewaschen und aus Wasser uni  kristallisiert.

   Auf diese Weise erhält man     N'-          4-Chlor-3-broinphenz-l-N'-n-propyl.biguanid    in  Form. seines     Monohydrochlorids,    welches bei  197 bis 198 C schmilzt.



  Process for the preparation of a biguanide derivative. The present invention relates to a process for the preparation of Nx-4-chloro-3- 1 # roniplienyl-N @ -n-propylbiguanide, which is a valuable chemotherapeutic agent or can be used as an intermediate for the preparation of chemotherapeutic agents. It is a particularly valuable antimalarial drug.



  According to the invention, the said new compound, namely Ni-4-chloro-3-broinpheny 1- N'-n-propylbiguanide, is obtained by reacting N'-n-propyldicyandiamide with 4-chloro-3-bromaniline.



  It is conveniently carried out by heating a salt of the amine with the sub-substituted dicyandiamide in the presence of a solvent, such as. B. water or ethoxyethanol.



  The Nl-4-chloro-3-bi-oniphen @ -1-N'-ii-propy 1-biguanid is a strong base which, with organic and inorganic acids, results in stable salts, which in some cases are easily soluble in water are. The salts can be prepared by dissolving the base in aqueous solutions of the acid and then evaporating the water, but they can be more conveniently prepared in dry form by mixing the components in an organic solvent, such as

   Acetone, ode @ - in an alcohol in which the salts are sparingly soluble, are produced. In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylenedisalylic acid, ethylenebis (3-oxy - na, phthoic acid and hydrochloric acid can be conveniently prepared.



  The following example serves to explain the invention.



  <I> Example: </I> A mixture of <B> 1.3.9 </B> parts of N@-n-Prop.##1- dicyandiainide and 24.3 parts of 4-chloro-3-bronianiline-chlorohydra. 75 parts of j3-ethoxyethanol are heated to boiling under reflux for 3 hours. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold ethyl acetate and crystallized from water.

   In this way, N'-4-chloro-3-broinphenz-1-N'-n-propyl.biguanide is obtained in the form. its monohydrochloride, which melts at 197 to 198 C.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur 11erstellttng von Ni-4-Chlor- 3.-bromphenyl-Ns-n-propylbiguanid, dadurch gekennzeichnet, dass man N'-n-Propyldicyan- diamid mit 4-Chlor-3-broma,nilin umsetzt. Das Ni-4-Chlor-3-bromphenyl-NI-n-propyl- bigttanid ist eine starke Base, deren 1Vlono- hydroehlorid bei 197 bis 198 C schmilzt. Die neue Base besitzt kräftige Antimalariaeigen- schaften. <B> PATENT CLAIM: </B> Process for the preparation of Ni-4-chloro-3.-bromophenyl-Ns-n-propylbiguanide, characterized in that N'-n-propyldicyanodiamide is mixed with 4-chloro-3- broma, nilin implements. Ni-4-chloro-3-bromophenyl-NI-n-propylbigttanide is a strong base, the 1Vlonohydrochloride melts at 197 to 198 ° C. The new base has powerful antimalarial properties.
CH259689D 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative. CH259689A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB259689X 1945-10-08
GB170946X 1946-09-17
CH254800T 1946-10-08

Publications (1)

Publication Number Publication Date
CH259689A true CH259689A (en) 1949-01-31

Family

ID=27178045

Family Applications (1)

Application Number Title Priority Date Filing Date
CH259689D CH259689A (en) 1945-10-08 1946-10-08 Process for the preparation of a biguanide derivative.

Country Status (1)

Country Link
CH (1) CH259689A (en)

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